MethylN-(4-{2-[(1S)-1-[(2E)-3-[5-chloro-2-(1H-1,2,3,4-tetrazol-1-yl)phenyl]prop-2-enamido]-2-phenylethyl]-pyridin-4-yl}phenyl)carbamate

ID: ALA3781319

Chembl Id: CHEMBL3781319

PubChem CID: 57976410

Max Phase: Preclinical

Molecular Formula: C31H26ClN7O3

Molecular Weight: 580.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Nc1ccc(-c2ccnc([C@H](Cc3ccccc3)NC(=O)/C=C/c3cc(Cl)ccc3-n3cnnn3)c2)cc1

Standard InChI:  InChI=1S/C31H26ClN7O3/c1-42-31(41)35-26-11-7-22(8-12-26)23-15-16-33-27(19-23)28(17-21-5-3-2-4-6-21)36-30(40)14-9-24-18-25(32)10-13-29(24)39-20-34-37-38-39/h2-16,18-20,28H,17H2,1H3,(H,35,41)(H,36,40)/b14-9+/t28-/m0/s1

Standard InChI Key:  ZBUQQUJRHVSUJI-CWBDRXANSA-N

Alternative Forms

1. Parent:

   

   ALA3781319

   Methyl ~{n}-[4-[2-[(1~{s})-1-[[(~{e})-3-[5-Chloranyl-2-(1,2,3,4-Tetrazol-1-Yl)phenyl]prop-2-Enoyl]amino]-2-Phenyl-Ethyl]pyridin-4-Yl]phenyl]carbamate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 580.05

Molecular Weight (Monoisotopic): 579.1786

AlogP: 5.67

#Rotatable Bonds: 9

Polar Surface Area: 123.92

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.98

CX Basic pKa: 4.03

CX LogP: 5.51

CX LogD: 5.51

Aromatic Rings: 5

Heavy Atoms: 42

QED Weighted: 0.22

Np Likeness Score: -1.39

References

1. Corte JR, Fang T, Pinto DJ, Orwat MJ, Rendina AR, Luettgen JM, Rossi KA, Wei A, Ramamurthy V, Myers JE, Sheriff S, Narayanan R, Harper TW, Zheng JJ, Li YX, Seiffert DA, Wexler RR, Quan ML..  (2016)  Orally bioavailable pyridine and pyrimidine-based Factor XIa inhibitors: Discovery of the methyl N-phenyl carbamate P2 prime group.,  24  (10): [PMID:27073051] [10.1016/j.bmc.2016.03.062]

2. Hu Z, Wang C, Han W, Rossi KA, Bozarth JM, Wu Y, Sheriff S, Myers JE, Luettgen JM, Seiffert DA, Wexler RR, Quan ML..  (2018)  Pyridazine and pyridazinone derivatives as potent and selective factor XIa inhibitors.,  28  (6): [PMID:29501396] [10.1016/j.bmcl.2018.02.049]

Source

Source(1):

• Scientific Literature